Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:08:40 UTC

Update Date

2021-09-26 23:12:25 UTC

HMDB ID

HMDB0256619

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pitolisant

Description

Pitolisant belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. Based on a literature review a significant number of articles have been published on Pitolisant. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pitolisant is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pitolisant is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0256619
     RDKit          3D
Pitolisant
 46 47  0  0  0  0  0  0  0  0999 V2000
    8.6120    1.5916   -1.3907 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0328    1.0464   -0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123    0.0365    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8008   -0.4035    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    0.1526    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990   -0.3525    0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7823   -1.5376   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842   -1.9598    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6108   -0.8461    0.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5506   -1.2746    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -0.2705    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1806    0.1307   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109    1.0868   -0.1103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8424    1.4119   -1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391    0.3928   -1.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318    0.3779   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2154   -0.0404    0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1100    0.9934    0.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6706    1.1594   -0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.6407   -1.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377   -0.3924    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151   -1.2014    1.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4863   -0.7133    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5225    0.4153    0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -1.2172   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276   -2.3371   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7280   -2.1858    1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235   -2.8264    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.1628    0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097   -1.5517    2.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    0.6655    1.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.7336    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247   -0.7299   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    0.6435   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1266    1.3229   -2.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089    2.4129   -1.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4720    0.7031   -2.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133   -0.6160   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033   -0.2536   -0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2238    1.4506   -0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9266    0.0870    1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288   -1.0684    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681    1.9798    1.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6400    0.9204    1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311    1.6099   -1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199    2.4429   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18 13  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
M  END


  Mrv1652310171623502D          

 20 21  0  0  0  0            999 V2000
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256619

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=C(CCCOCCCN2CCCCC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H26ClNO/c18-17-9-7-16(8-10-17)6-4-14-20-15-5-13-19-11-2-1-3-12-19/h7-10H,1-6,11-15H2

> <INCHI_KEY>
NNACHAUCXXVJSP-UHFFFAOYSA-N

> <FORMULA>
C17H26ClNO

> <MOLECULAR_WEIGHT>
295.85

> <EXACT_MASS>
295.1702922

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.49628513041506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{3-[3-(4-chlorophenyl)propoxy]propyl}piperidine

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
4.115267491666666

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.666484992010133

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
86.8124

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pitolisant

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0256619
     RDKit          3D
Pitolisant
 46 47  0  0  0  0  0  0  0  0999 V2000
    8.6120    1.5916   -1.3907 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0328    1.0464   -0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123    0.0365    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8008   -0.4035    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    0.1526    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990   -0.3525    0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7823   -1.5376   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842   -1.9598    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6108   -0.8461    0.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5506   -1.2746    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -0.2705    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1806    0.1307   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109    1.0868   -0.1103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8424    1.4119   -1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391    0.3928   -1.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318    0.3779   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2154   -0.0404    0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1100    0.9934    0.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6706    1.1594   -0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.6407   -1.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377   -0.3924    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151   -1.2014    1.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4863   -0.7133    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5225    0.4153    0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -1.2172   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276   -2.3371   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7280   -2.1858    1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235   -2.8264    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.1628    0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097   -1.5517    2.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    0.6655    1.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.7336    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247   -0.7299   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    0.6435   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1266    1.3229   -2.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089    2.4129   -1.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4720    0.7031   -2.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133   -0.6160   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033   -0.2536   -0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2238    1.4506   -0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9266    0.0870    1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288   -1.0684    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681    1.9798    1.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6400    0.9204    1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311    1.6099   -1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199    2.4429   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18 13  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 17-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-16         0                                  
HETATM    1  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -8.470   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.668  -8.470   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      -8.002  -6.160   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0256619
HETATM    1 CL1  UNL     1       8.612   1.592  -1.391  1.00  0.00          CL  
HETATM    2  C1  UNL     1       7.033   1.046  -0.807  1.00  0.00           C  
HETATM    3  C2  UNL     1       7.012   0.036   0.119  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.801  -0.403   0.592  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.596   0.153   0.150  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.299  -0.353   0.697  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.782  -1.538  -0.117  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.484  -1.960   0.530  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.611  -0.846   0.446  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.551  -1.275   1.091  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.657  -0.271   1.115  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.181   0.131  -0.231  1.00  0.00           C  
HETATM   13  N1  UNL     1      -3.211   1.087  -0.110  1.00  0.00           N  
HETATM   14  C11 UNL     1      -3.842   1.412  -1.338  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.939   0.393  -1.653  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.932   0.378  -0.520  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.215  -0.040   0.770  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.110   0.993   0.978  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.671   1.159  -0.777  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.877   1.641  -1.287  1.00  0.00           C  
HETATM   21  H1  UNL     1       7.938  -0.392   0.456  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.715  -1.201   1.320  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.486  -0.713   1.735  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.522   0.415   0.761  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.611  -1.217  -1.175  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.528  -2.337  -0.142  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.728  -2.186   1.589  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.024  -2.826   0.012  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.928  -2.163   0.532  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.310  -1.552   2.132  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.370   0.666   1.640  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.475  -0.734   1.740  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.425  -0.730  -0.891  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.325   0.643  -0.764  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.127   1.323  -2.193  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.309   2.413  -1.319  1.00  0.00           H  
HETATM   37  H17 UNL     1      -5.472   0.703  -2.569  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.513  -0.616  -1.847  1.00  0.00           H  
HETATM   39  H19 UNL     1      -6.803  -0.254  -0.702  1.00  0.00           H  
HETATM   40  H20 UNL     1      -6.224   1.451  -0.354  1.00  0.00           H  
HETATM   41  H21 UNL     1      -5.927   0.087   1.614  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.829  -1.068   0.700  1.00  0.00           H  
HETATM   43  H23 UNL     1      -4.668   1.980   1.023  1.00  0.00           H  
HETATM   44  H24 UNL     1      -3.640   0.920   1.979  1.00  0.00           H  
HETATM   45  H25 UNL     1       3.731   1.610  -1.135  1.00  0.00           H  
HETATM   46  H26 UNL     1       5.920   2.443  -2.023  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   20
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   19
CONECT    6    7   23   24
CONECT    7    8   25   26
CONECT    8    9   27   28
CONECT    9   10
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   18
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   17   39   40
CONECT   17   18   41   42
CONECT   18   43   44
CONECT   19   20   20   45
CONECT   20   46
END

HMDB0256619
     RDKit          3D
Pitolisant
 46 47  0  0  0  0  0  0  0  0999 V2000
    8.6120    1.5916   -1.3907 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0328    1.0464   -0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123    0.0365    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8008   -0.4035    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5958    0.1526    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990   -0.3525    0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7823   -1.5376   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842   -1.9598    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6108   -0.8461    0.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5506   -1.2746    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -0.2705    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1806    0.1307   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109    1.0868   -0.1103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8424    1.4119   -1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391    0.3928   -1.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318    0.3779   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2154   -0.0404    0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1100    0.9934    0.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6706    1.1594   -0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.6407   -1.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377   -0.3924    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151   -1.2014    1.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4863   -0.7133    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5225    0.4153    0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -1.2172   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276   -2.3371   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7280   -2.1858    1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235   -2.8264    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.1628    0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097   -1.5517    2.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695    0.6655    1.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.7336    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247   -0.7299   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    0.6435   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1266    1.3229   -2.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089    2.4129   -1.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4720    0.7031   -2.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133   -0.6160   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033   -0.2536   -0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2238    1.4506   -0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9266    0.0870    1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288   -1.0684    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681    1.9798    1.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6400    0.9204    1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311    1.6099   -1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199    2.4429   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18 13  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pitolisant	ChEMBL
BF2.649	ChEMBL
1-(3-(3-(4-Chlorophenyl)propoxy)propyl)piperidine	MeSH
Tiprolisant	MeSH

Chemical Formula

C₁₇H₂₆ClNO

Average Molecular Weight

295.85

Monoisotopic Molecular Weight

295.1702922

IUPAC Name

1-{3-[3-(4-chlorophenyl)propoxy]propyl}piperidine

Traditional Name

pitolisant

CAS Registry Number

Not Available

SMILES

ClC1=CC=C(CCCOCCCN2CCCCC2)C=C1

InChI Identifier

InChI=1S/C17H26ClNO/c18-17-9-7-16(8-10-17)6-4-14-20-15-5-13-19-11-2-1-3-12-19/h7-10H,1-6,11-15H2

InChI Key

NNACHAUCXXVJSP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Aryl chloride
Aryl halide
Piperidine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.47	ALOGPS
logP	4.12	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	86.81 m³·mol⁻¹	ChemAxon
Polarizability	35.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	170.032	30932474
DeepCCS	[M-H]-	167.674	30932474
DeepCCS	[M-2H]-	201.425	30932474
DeepCCS	[M+Na]+	176.357	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.4	32859911
AllCCS	[M+Na]+	174.3	32859911
AllCCS	[M-H]-	173.7	32859911
AllCCS	[M+Na-2H]-	174.3	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pitolisant	ClC1=CC=C(CCCOCCCN2CCCCC2)C=C1	2851.9	Standard polar	33892256
Pitolisant	ClC1=CC=C(CCCOCCCN2CCCCC2)C=C1	2174.9	Standard non polar	33892256
Pitolisant	ClC1=CC=C(CCCOCCCN2CCCCC2)C=C1	2193.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pitolisant GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9700000000-3dbad73168be1a49e119	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pitolisant GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pitolisant 10V, Positive-QTOF	splash10-0002-0590000000-81de9a6a39c65fd0dcef	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pitolisant 20V, Positive-QTOF	splash10-0f92-6920000000-9c9a86f5250502935877	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pitolisant 40V, Positive-QTOF	splash10-0f96-9700000000-bce3092a44893f241028	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pitolisant 10V, Negative-QTOF	splash10-0006-0490000000-07c881bceeacb79cc9c1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pitolisant 20V, Negative-QTOF	splash10-000x-4930000000-77ebf455bd0ade37ad3a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pitolisant 40V, Negative-QTOF	splash10-001i-9500000000-fa417cfa87d3c1e8a33d	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11642

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8123714

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pitolisant

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Pitolisant (HMDB0256619)

MOL for HMDB0256619 (Pitolisant)

3D MOL for HMDB0256619 (Pitolisant)

3D SDF for HMDB0256619 (Pitolisant)

3D-SDF for HMDB0256619 (Pitolisant)

PDB for HMDB0256619 (Pitolisant)

3D PDB for HMDB0256619 (Pitolisant)

SMILES for HMDB0256619 (Pitolisant)

INCHI for HMDB0256619 (Pitolisant)

Structure for HMDB0256619 (Pitolisant)

3D Structure for HMDB0256619 (Pitolisant)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra